US1810174A - Process for the production of condensation and polymerization products of acetylene - Google Patents
Process for the production of condensation and polymerization products of acetylene Download PDFInfo
- Publication number
- US1810174A US1810174A US2945A US294525A US1810174A US 1810174 A US1810174 A US 1810174A US 2945 A US2945 A US 2945A US 294525 A US294525 A US 294525A US 1810174 A US1810174 A US 1810174A
- Authority
- US
- United States
- Prior art keywords
- acetylene
- condensation
- production
- polymerization products
- mercury
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 title description 17
- 238000009833 condensation Methods 0.000 title description 15
- 230000005494 condensation Effects 0.000 title description 15
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 title description 15
- 238000006116 polymerization reaction Methods 0.000 title description 11
- 238000000034 method Methods 0.000 title description 10
- 238000004519 manufacturing process Methods 0.000 title description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- 239000000047 product Substances 0.000 description 13
- 229930195733 hydrocarbon Natural products 0.000 description 11
- 150000002430 hydrocarbons Chemical class 0.000 description 11
- 150000003839 salts Chemical class 0.000 description 10
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical class [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 8
- 229910052753 mercury Inorganic materials 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- 239000000839 emulsion Substances 0.000 description 5
- 229910052736 halogen Inorganic materials 0.000 description 5
- 125000005843 halogen group Chemical group 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- -1 xylo-l Chemical compound 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 229910052782 aluminium Chemical class 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical class [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000004411 aluminium Chemical class 0.000 description 3
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 229910021653 sulphate ion Inorganic materials 0.000 description 3
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 150000002730 mercury Chemical class 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- NUMXHEUHHRTBQT-AATRIKPKSA-N 2,4-dimethoxy-1-[(e)-2-nitroethenyl]benzene Chemical compound COC1=CC=C(\C=C\[N+]([O-])=O)C(OC)=C1 NUMXHEUHHRTBQT-AATRIKPKSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- RWVDMVCOVCFEJM-UHFFFAOYSA-N [Hg].C#C Chemical group [Hg].C#C RWVDMVCOVCFEJM-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- WKFSLMCSNKYSCL-UHFFFAOYSA-M benzenesulfonate;mercury(1+) Chemical compound [Hg+].[O-]S(=O)(=O)C1=CC=CC=C1 WKFSLMCSNKYSCL-UHFFFAOYSA-M 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- JJCFRYNCJDLXIK-UHFFFAOYSA-N cyproheptadine Chemical compound C1CN(C)CCC1=C1C2=CC=CC=C2C=CC2=CC=CC=C21 JJCFRYNCJDLXIK-UHFFFAOYSA-N 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G83/00—Macromolecular compounds not provided for in groups C08G2/00 - C08G81/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F10/00—Homopolymers and copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F38/00—Homopolymers and copolymers of compounds having one or more carbon-to-carbon triple bonds
- C08F38/02—Acetylene
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- C07C2531/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
Definitions
- condensation and polymerization products may be favored by heating and in many cases by the addltlon of activators, especially acids, alkalies and other substances of acid or basic reaction.
- Example I In 900 parts of glacial acetic acid 74 parts of acetate or mercury are dlssolved while warming. A solution of 77 parts of ben-' zene sulfonic acid in 100 parts of glacial acetic acid are allowed to flow into this hot liquid while stirring. Acetylene is intro symbolized into the emulsion of mercury benzene sulfonate formed in this way. A rapidabsorption ofacetylene takes place. On con tinuing the reaction the liquid becomes thicker. After the absorption of acetylene is finished the reaction mixture is heated for some time ata temperature of from 90 to 100 C. A semi-solid sticky mass is formed from which a resin-like substance is obtained by washing with water.
- Example I An emulsion is made by mixing 1000 parts of amyl alcohol and 50 parts of ground sulphate of mercury. Into this emulsion acetylone is introduced at a temperature of 110 C. until the absorption of acetylene which was very rapid at first, becomes slow. The reaction liquid becomes brownish in color and more viscous. It is then clarified by sedimentation and decantation. It can be .1 0 used directly as a lacquer or the resin formed by the reaction can be obtained in the solid state by distilling ofl the amyl alcohol.
- Example III Ewa/mple IV parts of sulphate of mercury are added to 1000 parts of hexane.
- acetylene Into this emulsion dried acetylene is introduced at a temperature of 50 C. while stirring. When the absorption of acetylene ceases the reaction mixture is heated for some hours using a reflux condenser. The excess of hexane" is distilled ofi by means of steam. The residue contains a solid resin.
- Process for the production of water insoluble condensation and polymerization products which consists in causing acetylene to react in the absence of water and in the presence of a catalytically acting salt selected from the group consisting of the salts arm mercury and alummium, upon a compound selected from the group consisting of hydrocarbons, halogen substituted hydrocarbons and aliphatic alcoliols and carrying the condensation beyond the stage of oily reaction products.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Phenolic Resins Or Amino Resins (AREA)
- Polymerization Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEC34362D DE493324C (de) | 1924-01-23 | 1924-01-23 | Verfahren zur Herstellung von Kondensationsprodukten des Acetylens |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US1810174A true US1810174A (en) | 1931-06-16 |
Family
ID=7021281
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US2945A Expired - Lifetime US1810174A (en) | 1924-01-23 | 1925-01-16 | Process for the production of condensation and polymerization products of acetylene |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US1810174A (de) |
| AT (1) | AT103106B (de) |
| DE (1) | DE493324C (de) |
| FR (1) | FR593338A (de) |
| GB (1) | GB228157A (de) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3207804A (en) * | 1959-08-06 | 1965-09-21 | Diamond Alkali Co | Non-conjugated polyacetylene and method of preparation |
| US4076926A (en) * | 1975-05-14 | 1978-02-28 | Imperial Chemical Industries Limited | Polymerization catalyst comprising aluminum halide and an alcohol or ether |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE747750C (de) * | 1934-10-20 | 1944-10-13 | Georg Kowalski Dr | Verfahren zur Herstellung von pech- bzw. harzartigen Kondensationsprodukten aus Steinkohlenteer, dessen Fraktionen oder Einzelbestandteilen und Acetylen |
| DE1246699B (de) * | 1960-05-17 | 1967-08-10 | Ciba Geigy | Verfahren zur Herstellung von Benzolkohlenwasserstoffen durch Cyclisierung von Acetylenkohlenwasserstoffen mittels Halogenide und/oder Oxyhalogenide des Tantals und/oderNiobs enthaltender Katalysatoren |
| DE1234700B (de) * | 1960-10-28 | 1967-02-23 | Ciba Geigy | Verfahren zur Herstellung von Benzolkohlenwasserstoffen durch Cyclisierung von Acctylenkohlenwasserstoffen mit Wolframhalogenide enthaltenden Katalysatoren |
-
1924
- 1924-01-23 DE DEC34362D patent/DE493324C/de not_active Expired
-
1925
- 1925-01-07 AT AT103106D patent/AT103106B/de active
- 1925-01-16 US US2945A patent/US1810174A/en not_active Expired - Lifetime
- 1925-01-17 GB GB1508/25A patent/GB228157A/en not_active Expired
- 1925-01-22 FR FR593338D patent/FR593338A/fr not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3207804A (en) * | 1959-08-06 | 1965-09-21 | Diamond Alkali Co | Non-conjugated polyacetylene and method of preparation |
| US4076926A (en) * | 1975-05-14 | 1978-02-28 | Imperial Chemical Industries Limited | Polymerization catalyst comprising aluminum halide and an alcohol or ether |
Also Published As
| Publication number | Publication date |
|---|---|
| DE493324C (de) | 1930-03-12 |
| FR593338A (fr) | 1925-08-20 |
| GB228157A (en) | 1926-07-19 |
| AT103106B (de) | 1926-04-26 |
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